Tax Tips For Procrastinators, And You Know Who You Are

A customer goes over tax documents at a post office in New York City on last year's Tax Day.

Justin SullivanGetty Images

Originally published on April 15, 2013 12:40 pm

Still haven't filed your taxes, eh?

Well, you have until 11:59 p.m. Monday to get it all done — or at least file for an extension that gets you off the hook until Oct. 15. To help all of you procrastinators, here are answers to a few of your questions.

If I'm filing by mail, can I come skidding into the post office at 11:58 p.m. and still make the deadline?

Maybe — depending on where you live. Most post office locations will keep regular hours; some will stay open until 7 p.m. or 8 p.m. to make sure tax returns get postmarked before midnight. And a few — very few — will stay open until midnight to let the extreme procrastinators get a postmark stamped by 11:59 p.m.

And the IRS says that to submit a valid filing, your envelope not only has to make the postmark deadline, but it also has to have the correct address and enough postage.

These days, most people file electronically. What's the deadline for that?

The IRS says your tax return must be time stamped by an IRS-authorized electronic-return transmitter by 11:59 p.m. Fortunately, those transmitters take into account your time zone. So taxpayers in Boston have a midnight deadline and so do those in Seattle — even though there is a three-hour difference between the two cities.

I hate doing my taxes. Can I make it more fun by taking my laptop to a coffee shop? The flow of caffeine helps keep my mind sharp.

Security experts say it's a bad idea to transmit important financial information using a public Wi-Fi connection. A public network makes it easier for bad actors to be listening in and intercepting your personal data.

And don't file from your work computer either. You never know — there could be an unscrupulous network administrator who is electronically looking over your shoulder to spot your Social Security number. It's best to do your taxes at home.

And one more thing: Don't have a lot of browser tabs open when you are filling in your tax forms. You don't want to have spyware infecting one window while you are trying to file your information with the IRS in another.

I give up. I really won't have time to get my taxes figured out by 11:59 p.m. Monday. What can I do?

It's easy to file for an extension to give yourself an extra six months. There's no harm in it — roughly 140 million people file tax returns each year, and nearly 11 million will ask for an extension. No biggie.

But here's the important thing to remember: Pushing back the filing deadline doesn't change the pay-your-taxes deadline. You owe your tax payment to the IRS by April 15, and if you don't pony up, you could face interest payments and penalties on what you owe.

If you are like most people and have a tax refund coming to you, then it doesn't hurt to file for an extension. It only delays the arrival of your annual refund check. If you don't mind waiting, then neither does the IRS.

If you owe money to the IRS, then do your best to estimate the amount and send it in. And if you just can't afford to pay your taxes now, you may qualify for a payment plan or other relief. The important thing is to file and let IRS officials know you are trying to deal with your situation, not hiding from the tax man.